UREA-TERMINATED ETHER POLYURETHANES AND AQUEOUS DISPERSIONS THEREOF

• US 20090259012A1
• Filed: 12/03/2008
• Published: 10/15/2009
• Est. Priority Date: 12/10/2007
• Status: Abandoned Application

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: ROBERTS, C. CHAD
• Application Number:
  US12/327,194
• Publication Number:
  US 20090259012A1
• Time in Patent Office: Days
• US Class Current: 528/66
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/2865 Compounds having only one primary or secondary amino group; Ammonia
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/4854 Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/6692 with compounds of group C08G18/34
• CPC Class Codes: C08G 18/765 alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C09D 11/30 Inkjet printing inks

Abstract

The present invention relates to water-dispersible urea terminated ether type polyurethanes based on polyether diols, aqueous dispersions of such polyurethanes, and their manufacture. The urea termination can have nonionic hydrophilic substituents.

Claims

1. An aqueous dispersion of a polyurethane composition comprising at least one compound of the general structure (I):

R₁=alkyl, substituted alkyl, substituted alkyl/aryl from a diisocyanate,

R₂=alkyl, substituted/branched alkyl from a diol,

R₃=alkyl, a non-isocyanate reactive substituted/branched alkyl from an amine terminating group,

R₄=hydrogen, alkyl, a non-isocyanate reactive substituted/branched alkyl from the amine terminating group;

n=2 to 30;

and where R₂=Z₁ or Z₂ and at least one Z₁ and at least one Z₂ must be present in the polyurethane composition;

m greater than or equal to 3 to about 12,

p greater than or equal to 2,

R₅, R₆=hydrogen, alkyl, substituted alkyl, aryl;

where the R₅ is the same or different with each —

CR₅R₆;

where R₅ and R₅ or R₆ can be joined to form a cyclic structure;

Z₂ is a diol substituted with an ionic group;

wherein the urea content of the urea-terminated polyurethane is at least 2 wt % of the polyurethane and at most about 14 wt % of the polyurethane.

2. The polyurethane of claim 1 where the urea terminated polyurethane part of the polyurethane is at least 2.5 wt % and at most 10.5 wt %

3. The polyurethane of claim 1 where the polyether diol of Structure II is at least 50 weight percent of the polyether diol.

4. The polyurethane of claim 1 where the polyether diol of Structure II is at least 75 weight percent of the polyether diol.

5. The polyurethane of claim 1 where the polyether diol of Structure II is at least 90 weight percent of the polyether diol.

6. The polyurethane of claim 1 where the polyether diol of Structure II has a number average molecular weight of 200 to 5000.

7. The polyurethane of claim 1 where the polyether diol of Structure II has a number average molecular weight of 240 to 3600.

8. The polyurethane of claim 1 where the polyether diol of Structure II has m=3 or 4.

9. The polyurethane of claim 8 where R₅ and R₆ are hydrogen.

10. The polyurethane of claim 1 where the polyether diol of Structure II m=3 and the ether is group is derived from biochemical transformations.

11. The polyurethane of claim 1 where Groups R₃ and R₄ are alkyl.

12. The polyurethane of claim 1 where Groups R₃ and R₄ are substituted with nonionic hydrophilic groups.

13. The polyurethane of claim 1 where Groups R₃ and R₄ are methoxyethyl.

14. The polyurethane composition of claim 1 where the ionic content of the polyurethane is 10 to 210 milliequivalents per 100 g of polyurethane.

15. The polyurethane composition of claim 1 where the ionic content of the polyurethane is 20 to 140 milliequivalents per 100 g of polyurethane.

16. A method of preparation of a polyurethane composition comprising a urea terminated polyurethane comprising the steps:

(a) providing reactants comprising (i) at least one diol Z₁ (ii) at least one polyisocyanate component comprising a diisocyanate, and (iii) at least one hydrophilic reactant comprising at least one isocyanate reactive ingredient containing an ionic group, Z₂;

(b) contacting (i), (ii) and (iii) in the presence of a water-miscible organic solvent to form an isocyanate-functional polyurethane prepolymer;

(c) adding water to form an aqueous dispersion; and

(d) prior to, concurrently with or subsequent to step (c), chain-terminating the isocyanate-functional prepolymer with a primary or secondary amine.